Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds

The combination of the Sharpless asymmetric epoxidation reaction with a sulfur ylide mediated synthesis of allylic alcohols from epoxides provides a powerful iterative process for the production of polyoxygenated compounds. The alkene installed in the sulfur ylide reaction has also been used in a number of ring closing metathesis reactions to produce highly oxygenated cyclic compounds.